Hydrochloric Acid → HCID 19611729, compound

Participants

Reaction Steps

159 mg of N-(methoxycarbonylmethyl)-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine in 5 ml of tetrahydrofuran was stirred together with 0.3 ml of 4N aqueous sodium hydroxide at room temperature for 1.5 hours. The reaction solution was acidified with 1N hydrochloric acid and then extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in 3 ml of dimethylformamide and stirred together with 161 mg of aniline and 98 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride at room temperature for 17 hours. After addition of water, the reaction solution was extracted with ethyl acetate, and the extract was washed with 1N aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5717; hexane/ethyl acetate=1/1] to give 102 mg of the title compound as a colorless foamy substance.

Provenance & Evidence